159505-85-8

Basic information

• Product Name: FMOC-D-PHE-OPFP
• Synonyms: FMOC-D-PHENYLALANINE PENTAFLUOROPHENYL ESTER;FMOC-D-PHE-OPFP;N-ALPHA-FMOC-D-PHENYLALANINE PENTAFLUOROPHENYL ESTER;(9H-Fluoren-9-yl)MethOxy]Carbonyl D-Phe-OPfp
• CAS NO: 159505-85-8
• Molecular Formula: C30H20F5NO4
• Molecular Weight: 553.48
• Product Categories: Fmoc-Amino Acids and Derivatives;Fmoc-Amino acid series
• Mol File: 159505-85-8.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• Storage Temp.: Store at 0°C
• CAS DataBase Reference: FMOC-D-PHE-OPFP(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-D-PHE-OPFP(159505-85-8)
• EPA Substance Registry System: FMOC-D-PHE-OPFP(159505-85-8)

Safety Data

• Hazardous Substances Data: 159505-85-8(Hazardous Substances Data)

Usage

General Description

FMOC-D-PHE-OPFP is a chemical compound most commonly used in peptide synthesis as a protecting group for the amino acid phenylalanine. The compound consists of a fluorenylmethyloxycarbonyl (FMOC) group attached to the D form of phenylalanine and also an ortho-pentafluorophenyl (OPFP) ester moiety. The FMOC group protects the amino group of phenylalanine during peptide synthesis, allowing for selective deprotection when needed. The OPFP ester, on the other hand, provides stability and protection to the carboxyl group of the amino acid. Together, FMOC-D-PHE-OPFP is a useful chemical tool in the manufacturing of peptides with specific sequences and functions.

Upstream product

• 88744-04-1 (9-fluorenyl)methyl pentafluorophenyl carbonate 
• 63-91-2 L-phenylalanine 
• 35661-40-6 N-Fmoc L-Phe 
• 771-61-9 2,3,4,5,6-pentafluorophenol 
• 244633-31-6 pentafluorophenyl 4-nitrobenzenesulfonate 
• 96157-57-2 bis(pentafluorophenyl)sulfite 
• 14533-84-7 pentafluorophenyl trifloroacetate 
• 103321-57-9 2S-flouren-9-ylmethoxycarbonylamino-3-phenylpropionyl chloride 

Downstream Products

• 252570-73-3 C₆₉H₁₀₄N₁₈O₁₅S 
• 1656305-20-2 Fmoc-FCit-PAB-OH 
• 960237-92-7 Fmoc-Phe-Phe-pyVal-Ala-Ser(t-Bu)-OH 

Relevant articles and documents

Synthesis of aryl esters of protected amino acids from aryl sulfonates

Aryl esters of Boc- and Fmoc-protected amino acids derived from electron-deficient phenols have been prepared in good yields from aryl 4- nitrobenzenesulfonates in the presence of 1-hydroxy-benzotriazole as catalyst.

PREPARATION OF PENTAFLUOROPHENYL ESTERS OF FMOC PROTECTED AMINO ACIDS WITH PENTAFLUOROPHENYL TRIFLUOROACETATE

A high yield procedure for the preparation of pentafluorophenyl esters of Nα-9-fluorenylmethyloxycarbonyl protected amino acids is described.The procedure utilizes pentafluorophenyl trifluoroacetate.

9-Fluorenylmethyl Pentafluorophenyl Carbonate as a Useful Reagent for the Preparation of N-9-Fluorenylmethyloxycarbonylamino Acids and their Pentafluorophenyl Esters

9-Fluorenylmethyl pentafluorophenyl carbonate is a useful reagent for the efficient, side reaction-free introduction of N-9-fluorenylmethyloxycarbonyl protecting group into amino acids and for the subsequent preparation of their pentafluorophenyl esters.Some new compounds of both types are described.